K. Kobayashi, Hiroto Tanaka, Harumi Takabatake
May 15, 1999
Citations
0
Influential Citations
10
Citations
Journal
Bulletin of the Chemical Society of Japan
Abstract
The reaction of 2-(lithiomethyl)benzonitrile with 2-phenylthio-2-alkenoic acid derivatives in diglyme at −78 °C, followed by oxidation with sodium metaperiodate in aqueous MeOH at room temperature and the subsequent elimination reaction in refluxing toluene, gave 4-(2-cyanophenyl)-2-butenoic acid derivatives in moderate-to-fair overall yields. Intramolecular cyclization of these products using NaH in DMF at 0 °C gave 1-amino-2-naphthalenecarboxylic acid derivatives almost quantitatively. Successive treatments with an isocyanate without isolation of the aminonaphthalenecarboxylates under reflux afforded benzo[h]quinazoline-2,4(1H,3H)-diones in moderate-to-good yields.